Curable polyurea forming composition, method of making, and composite article

Patent metadata

Field	Value
Publication number	US-9587139-B2
Application number	US-201314399254-A
Country	US
Kind code	B2
Filing date	Jun 4, 2013
Priority date	Jun 15, 2012
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

A curable composition includes: a) at least one aliphatic polyisocyanate; b) at least one aliphatic polyamine; and c) from 8 to 17 percent by weight of at least one liquid compound, based on the total weight of components a), b) and c) combined. Each liquid compound is independently represented by the formula (I): wherein Z represents an n valent organic group, and n represents an integer ≧1. Methods of coating the curable coating on a substrate and composite articles are also disclosed.

First claim

What is claimed is:

1. A curable composition comprising components:
a) at least one aliphatic polyisocyanate;
b) at least one aliphatic polyamine; and
c) from 8 to 17 percent by weight of at least one liquid compound, based on the total weight of components a), b) and c) combined, wherein each compound of said at least one liquid compound is independently represented by the formula:

wherein Z represents an n-valent organic group, and
n represents an integer ≧1.

2. The curable composition of claim 1 , wherein Z represents —CH 2 OH or —C(═O)OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OC(═O)—.

3. The curable composition of claim 1 , wherein said at least one aliphatic polyamine comprises an aspartic ester.

4. The curable composition of claim 1 , wherein said at least one aliphatic polyamine includes an aliphatic polyamine represented by the formula

wherein R 1 and R 2 independently represent an alkyl group having 1 to 10 carbon atoms, and R 3 , R 4 , R 5 , and R 6 independently represent hydrogen or an alkyl group having 1 to 5 carbon atoms.

5. The curable composition of claim 4 , wherein R 1 and R 2 are independently alkyl groups comprising at least 2 carbon atoms.

6. The curable composition of claim 1 , wherein each said at least one aliphatic polyamine has the general formula:

wherein R 7 and R 8 independently represent an alkyl group having from 1 to 10 carbon atoms, or a cyanoalkyl group having from 1 to 10 carbon atoms, and wherein R 9 , R 10 , and R 11 are independently hydrogen or an alkyl group having from 1 to 5 carbon atoms.

7. The curable composition of claim 1 , wherein the at least one aliphatic polyisocyanate comprises a trimer of 1,6-hexanediisocyanate.

8. A method of coating a substrate, the method comprising coating a curable composition onto a surface of a substrate, and at least partially curing the curable composition, wherein the curable composition comprises components:
a) at least one aliphatic polyisocyanate;
b) at least one aliphatic polyamine; and
c) from 8 to 17 percent by weight of at least one liquid compound, based on the total weight of components a), b) and c) combined, wherein each compound of said at least one liquid compound is independently represented by the formula:

wherein Z represents an n-valent organic group, and
n represents an integer ≧1.

9. The method of claim 8 , wherein Z represents —CH 2 OH or —C(═O)OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OC(═O)—.

10. The method of claim 8 , wherein said at least one aliphatic polyamine comprises an aspartic ester.

11. The method of claim 8 , wherein said at least one aliphatic polyamine includes an aliphatic polyamine represented by the general formula

wherein R 1 and R 2 independently represent an alkyl group having 1 to 10 carbon atoms, and R 3 , R 4 , R 5 , and R 6 independently represent hydrogen or an alkyl group having 1 to 5 carbon atoms.

12. The method of claim 8 , wherein each said at least one aliphatic polyamine has the general formula:

wherein R 7 and R 8 independently represent an alkyl group having from 1 to 10 carbon atoms, or a cyanoalkyl group having from 1 to 10 carbon atoms, and wherein R 9 , R 10 , and R 11 are independently hydrogen or an alkyl group having from 1 to 5 carbon atoms.

13. The method of claim 8 , wherein the at least one aliphatic polyisocyanate comprises a trimer of 1,6-hexanediisocyanate.

14. A composite article comprising a coating disposed on a substrate, wherein the
coating is prepared from components comprising:
a) at least one aliphatic polyisocyanate;
b) at least one aliphatic polyamine; and
c) from 8 to 17 percent by weight of at least one liquid compound, based on the total weight of components a), b) and c) combined, wherein each compound of said at least one liquid compound is independently represented by the formula:

wherein Z represents an n-valent organic group, and
n represents an integer ≧1.

15. The composite article of claim 14 , wherein Z represents —CH 2 OH or —C(—O)OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OC(═O)—.

16. The composite article of claim 14 , wherein said at least one aliphatic polyamine comprises an aspartic ester.

17. The composite article of claim 14 , wherein said at least one aliphatic polyamine includes an aliphatic polyamine represented by the general formula

wherein R 1 and R 2 independently represent an alkyl group having 1 to 10 carbon atoms, and R 3 , R 4 , R 5 , and R 6 independently represent hydrogen or an alkyl group having 1 to 5 carbon atoms.

18. The composite article of claim 14 , wherein each said at least one aliphatic polyamine has the general formula:

wherein R 7 and R 8 independently represent an alkyl group having from 1 to 10 carbon atoms, or a cyanoalkyl group having from 1 to 10 carbon atoms, and wherein R 9 , R 10 , and R 11 are independently hydrogen or an alkyl group having from 1 to 5 carbon atoms.

19. The composite article of claim 14 , wherein the at least one aliphatic polyisocyanate comprises a trimer of 1,6-hexanediisocyanate.

Assignees

• 3M Innovative Properties Co

Inventors

• Kugel Alexander J
• Jones Clinton L
• Apel Cori S
• Prince Ryan B

Classifications

• C08G18/282

  Alkanols, cycloalkanols or arylalkanols including terpenealcohols · CPC title

• C08G18/3821

  Carboxylic acids; Esters thereof with monohydroxyl compounds · CPC title

• Y10T428/31551

  Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.] · CPC title

• C08G18/3234

  cycloaliphatic · CPC title

• C08G2150/50

  Compositions for coatings applied by spraying at least two streams of reaction components · CPC title